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New phenanthridine derivatives as bradykinin antagonists

A technology for bradykinin and phenanthridine, which is applied in the field of phenanthridine derivatives as bradykinin antagonists, and can solve problems such as unclear function, involvement in pain transmission and hyperalgesia.

Inactive Publication Date: 2012-10-10
RICHTER GEDEON NYRT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The function of these receptors is unknown, but they have been implicated in pain transmission and hyperalgesia

Method used

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  • New phenanthridine derivatives as bradykinin antagonists
  • New phenanthridine derivatives as bradykinin antagonists
  • New phenanthridine derivatives as bradykinin antagonists

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0197] 2-[5-(3,4-dichloro-benzenesulfonyl)-8-fluoro-5,6-dihydro-phenanthridine-6-yl]-N-{2-[4-(4,5- Dihydro-1H-imidazol-2-yl)-phenyl]-ethyl}-acetamide hydrochloride

[0198] a) 4′-Fluoro-biphenyl-2-ylamine

[0199] To a stirred solution of 2-bromoaniline (1.72 g, 10.0 mmol) in diglyme (30 mL) was added tetrakis(triphenylphosphine)-palladium(0) (0.13 g, 0.3 mmol) and 2.0 M Aqueous sodium carbonate solution (15 mL, 30.0 mmol). In a separate flask, 4-fluorophenylboronic acid (2.23 g 16.0 mmol) was dissolved in ethanol (8 mL), and the mixture containing 2-bromoaniline was added to the boronic acid solution. The resulting brown reaction mixture was heated at 80°C for 6 hours, then cooled, diluted with ethyl acetate and washed with saturated ammonium chloride solution. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and n-hexane: ethyl a...

Embodiment 2

[0210] 2-[5-(3,4-Dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridine-6-yl]-N-{2-[4-(4,5-dihydro-1H -imidazol-2-yl)-phenyl]-ethyl}-acetamide hydrochloride

[0211] a) N-biphenyl-2-yl-3,4-dichloro-benzenesulfonamide

[0212] The title compound was prepared from 2-aminobiphenyl (Aldrich) according to the method described in Example 1b.

[0213] b) [5-(3,4-Dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridin-6-yl]-acetic acid methyl ester

[0214] The title compound was prepared from N-biphenyl-2-yl-3,4-dichloro-benzenesulfonamide according to the method described in Example 1c.

[0215] c) [5-(3,4-Dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridin-6-yl]-acetic acid

[0216] The title compound was prepared from [5-(3,4-dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridin-6-yl]-acetic acid methyl ester according to the method described in Example 1d.

[0217] d) 2-[5-(3,4-Dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridine-6-yl]-N-{2-[4-(4,5-dihydro-1H -imidazol-2-y...

Embodiment 3

[0220] 2-[5-(3,4-Dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridine-6-yl]-N-[2-(4-pyridin-4-yl-piperazine- 1-yl)-ethyl]-acetamide

[0221] According to the method described in Example 1e, from [5-(3,4-dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridine-6-yl]-acetic acid (Example 2c) and 2- (4-Pyridin-4-yl-piperazin-1-yl)-ethylamine (refer to Example 1) to prepare the title compound. MS(EI)637.3(MH + ).

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Abstract

The present invention relates to new phenanthridine derivatives of formula (I), to the processes for producing the same, to pharmacological compositions containing the same and to their use in therapy or prevention of painful and inflammatory processes.

Description

field of invention [0001] The present invention relates to novel phenanthridine derivatives of formula (I) and their optical enantiomers or racemates and / or salts and / or hydrates and / or solvates, which can be used for the treatment or prevention of pain and inflammation process. The invention also relates to processes for the production of compounds of formula (I) and pharmacological compositions containing them. Background of the invention [0002] Kinins are endogenous peptides formed in plasma and peripheral tissues following kallikrein-catalyzed cleavage of kininogen in response to tissue injury or infection. Kinins play an important role in the pathophysiological processes that accompany pain and inflammation. Their biological actions are mediated by 2 G-protein coupled membrane receptors denoted B1 and B2. B1 and B2 receptors have been cloned [Biochem. Biophys. Res. Commun., 184 (1992) 260-268 and J. Biol. Chem., 269 (1994) 21583-21586], regulate their expression, s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/74C07D401/12C07D221/12C07D401/14C07D295/12A61K31/473C07D401/10A61P25/02
CPCC07D401/14C07D401/12C07D213/74C07D295/135C07D401/10C07D221/12A61P25/02A61P25/04A61P29/00A61P43/00A61K31/473C07D295/12
Inventor G·贝克E·鲍佐G·茨兹拉J·埃勒斯S·法卡斯K·豪诺克E·施密特E·斯泽恩特梅I·瓦高M·瓦斯塔格
Owner RICHTER GEDEON NYRT